Reduction of two isomeric oximes of aryl alkyl 1,2-diketones: Difference in products formed in polarography and controlled potential electrolysis

At pH lower than 5 under conditions of d.c. polarography and cyclic voltammetry the oxime PhCOC(=NOH)CH3 does not yield the expected reducible α-aminoketone, but rather a non-reducible olefin derivative. Its formation is attributed to a reduction of a diprotonated form of a ketoimine intermediate. In the same pH-range under conditions of controlled potential electrolysis the olefin derivative is slowly converted in a homogeneous reaction into a reducible α-aminoketone.